Cumene-to-phenol process

Cumene hydroperoxide (CHP) formation.

The formation of the hydroperoxide proceeds by a free radical chain reaction. A radical initiator abstracts a hydrogenfree radical from the
molecule, creating a tertiary free radical. The creation of the tertiary free radical is the initial step in the reaction.

The free radical is attracted to an oxygen molecule. This attraction produces the hydroperoxide free radical.

The hydroperoxide free radical abstracts a hydrogen free radical from a second molecule of cumene to form cumene hydroperoxide and
a new tertiary free radical.

Cumene hydroperoxide degradation.

The degradation of the cumene hydroperoxide proceeds via a carbocation mechanism. In the first step, a pair of electrons on the oxygen
of the hydroperoxide's hydroxyl group is attracted to a proton of the H3O+ molecule, forming an oxonium ion.

The oxonium ion becomes stabilized when the positively charged oxygen leaves in a water molecule. This loss of a water molecule
produces a new oxonium ion.

A phenide ion shift to the oxygen atom (which creates a tertiary carbocation) stabilizes the positively charged oxygen. (A phenide ion is a
phenyl group with an electron bonding pair available to form a new bond to the ring.)

 The carbocation is stabilized by an acidbase reaction with a water molecule, leading to the formation of an oxonium ion.

The loss of a proton stabilizes the oxonium ion.

A proton is picked up by the ether oxygen in an acidbase reaction, yielding a new oxonium ion.

The positively charged ether oxygen pulls the electrons in the oxygencarbon bond toward itself, thus delocalizing the charge over both
of the atoms. The partial positive charge on the carbon attracts the nonbonding electron pair from the oxygen of the OH group, allowing the
electrons in the original oxygencarbon bond to be released back to the more electronegative oxygen atom.

A proton is lost from the protonated acetone molecule, leading to the formation of acetone.

Source : http://www.cliffsnotes.com/sciences/chemistry/organic-chemistry-ii/phenols-and-aryl-halides/synthesis-of-phenols

Production of phenol in the future (additional slide)

phenol cumene-to-phenol process acetone 6 phenol 10 acetone
() phenol acetone 2-3 phenol
benzene 1 ok oxidation benzene nitrogen (I) oxide (nitrous oxide), N2O:
Nitrous oxide gaseous by-product polyamide 6,6 greenhouse gas
gas phase 570-720 K zeolite 95% benzene phenol
** lab (January 2,2014)
Source : http://www.essentialchemicalindustry.org/chemicals/phenol.html